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ISSN: 2056-9890

2,3,4,6-Tetra-O-acetyl-1-O-(4-meth­oxy­cinnamo­yl)-β-D-gluco­pyran­ose

aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
*Correspondence e-mail: zhuhj@njut.edu.cn

(Received 22 January 2008; accepted 18 February 2008; online 22 February 2008)

Mol­ecules of the title compound, C24H28O12, are linked by inter­molecular C—H⋯O hydrogen bonds. Bond lengths and angles are normal.

Related literature

For related literature, see: Loganathan & Trivedi (1987[Loganathan, D. & Trivedi, G. K. (1987). Carbohydr. Res. 162, 117-125.]); Yu et al. (1991[Yu, C. F., Liu, Z. F. & Cai, M. S. (1991). Chem. Res. Chin. Univ. 12, 349-350.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C24H28O12

  • Mr = 508.46

  • Monoclinic, P 21

  • a = 9.972 (2) Å

  • b = 6.0580 (12) Å

  • c = 21.680 (4) Å

  • β = 97.19 (3)°

  • V = 1299.4 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 298 (2) K

  • 0.40 × 0.10 × 0.10 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.959, Tmax = 0.990

  • 2955 measured reflections

  • 2790 independent reflections

  • 1578 reflections with I > 2σ(I)

  • Rint = 0.062

  • 3 standard reflections every 200 reflections intensity decay: none

Refinement
  • R[F2 > 2σ(F2)] = 0.070

  • wR(F2) = 0.189

  • S = 1.02

  • 2790 reflections

  • 319 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.43 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C5—H5A⋯O3i 0.96 2.45 3.164 (12) 131
C10—H10A⋯O5ii 0.98 2.48 3.423 (9) 160
C13—H13A⋯O11iii 0.98 2.55 3.371 (8) 142
C24—H24A⋯O8iv 0.96 2.51 3.457 (10) 171
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+1]; (ii) x, y+1, z; (iii) x, y-1, z; (iv) [-x+1, y+{\script{1\over 2}}, -z].

Data collection: CAD-4 Software (Enraf–Nonius, 1985[Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

1-O-(p-methoxycinnamoyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose is a type of glycolipid derivative (Loganathan et al., 1987) that plays an important role in medical applications, such as anti-tumor and antibacterial applications. We report here the crystal structure of the title compound, (I).

The molecular structure of (I) is shown in Fig. 1. The bond lengths and angles are within normal ranges (Allen et al., 1987).

In the crystal, molecules are linked to each other to form a three dimensional framework via intermolecular C—H···O hydrogen bonds.

Related literature top

For related literature, see: Loganathan & Trivedi (1987); Yu et al. (1991). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound, (I), was prepared by a method similar to that reported previously (Yu et al., 1991). The crystals were obtained by dissolving compound I (1.5 g) in methanol (25 ml) and evaporating the solvent slowly at room temperature for about 10 d.

Refinement top

H atoms were positioned geometrically, with O—H = 0.82 and C—H = 0.93Å for aromatic H, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C/O), where x = 1.2 for aromatic H and x = 1.5 for other H. In the absence of significant anomalous scattering effects 82 Friedel pairs have been merged.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A drawing of the title molecular structure, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown by dashed lines.
2,3,4,6-Tetra-O-acetyl-1-O-(4-methoxycinnamoyl)-β-D-glucopyranose top
Crystal data top
C24H28O12F(000) = 536
Mr = 508.46Dx = 1.300 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 9.972 (2) Åθ = 9–12°
b = 6.0580 (12) ŵ = 0.11 mm1
c = 21.680 (4) ÅT = 298 K
β = 97.19 (3)°Needle, colourless
V = 1299.4 (4) Å30.40 × 0.10 × 0.10 mm
Z = 2
Data collection top
Enraf–Nonius CAD-4
diffractometer
1578 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.062
Graphite monochromatorθmax = 26.0°, θmin = 1.9°
ω/2θ scansh = 1111
Absorption correction: ψ scan
(North et al., 1968)
k = 07
Tmin = 0.959, Tmax = 0.990l = 026
2955 measured reflections3 standard reflections every 200 reflections
2790 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.09P)2]
where P = (Fo2 + 2Fc2)/3
2790 reflections(Δ/σ)max < 0.001
319 parametersΔρmax = 0.43 e Å3
1 restraintΔρmin = 0.40 e Å3
Crystal data top
C24H28O12V = 1299.4 (4) Å3
Mr = 508.46Z = 2
Monoclinic, P21Mo Kα radiation
a = 9.972 (2) ŵ = 0.11 mm1
b = 6.0580 (12) ÅT = 298 K
c = 21.680 (4) Å0.40 × 0.10 × 0.10 mm
β = 97.19 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
1578 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.062
Tmin = 0.959, Tmax = 0.9903 standard reflections every 200 reflections
2955 measured reflections intensity decay: none
2790 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0701 restraint
wR(F2) = 0.189H-atom parameters constrained
S = 1.02Δρmax = 0.43 e Å3
2790 reflectionsΔρmin = 0.40 e Å3
319 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5843 (6)0.1875 (12)0.2849 (3)0.089
C10.6777 (7)0.468 (2)0.3547 (4)0.099 (3)
H1A0.76430.42700.34330.148*
H1B0.68040.46170.39900.148*
H1C0.65590.61530.34050.148*
O20.4512 (4)0.3681 (9)0.3422 (2)0.0591 (13)
C20.5738 (7)0.3138 (18)0.3256 (4)0.084 (3)
O30.2760 (6)0.0744 (11)0.4807 (2)0.0799 (17)
C30.3974 (9)0.2530 (17)0.4674 (4)0.090 (3)
H3A0.39750.27270.51130.135*
H3B0.48880.24450.45800.135*
H3C0.35260.37580.44570.135*
O40.3228 (5)0.0182 (9)0.38543 (19)0.0567 (12)
C40.3267 (7)0.0507 (14)0.4480 (3)0.0567 (18)
O50.0717 (7)0.2870 (10)0.3886 (3)0.0846 (18)
C50.0937 (9)0.123 (2)0.4448 (4)0.116 (4)
H5A0.10260.26750.46190.174*
H5B0.17950.07580.42390.174*
H5C0.06410.02120.47760.174*
O60.0213 (4)0.0758 (8)0.3744 (2)0.0512 (12)
C60.0086 (8)0.1292 (15)0.3991 (3)0.061 (2)
O70.1160 (7)0.2286 (11)0.2512 (3)0.095 (2)
C70.0606 (8)0.2633 (14)0.1464 (3)0.070 (2)
H7A0.07390.41810.15280.106*
H7B0.03050.23820.13810.106*
H7C0.12240.21370.11160.106*
O80.0694 (5)0.0730 (8)0.1983 (2)0.0547 (12)
C80.0852 (7)0.1400 (14)0.2026 (4)0.0600 (19)
O90.1321 (4)0.3455 (8)0.24191 (19)0.0492 (11)
C90.0883 (6)0.2144 (13)0.2493 (3)0.0539 (18)
H9A0.14310.13880.27670.065*
H9B0.13680.34580.23370.065*
O100.3339 (4)0.4790 (8)0.2226 (2)0.0546 (12)
C100.0445 (6)0.2813 (12)0.2859 (3)0.0521 (18)
H10A0.02880.40980.31150.062*
C110.1097 (6)0.1011 (11)0.3280 (3)0.0482 (17)
H11A0.11500.03660.30470.058*
O110.2593 (5)0.8310 (8)0.2125 (2)0.0652 (14)
O120.8530 (5)0.5383 (9)0.0491 (2)0.0678 (15)
C120.2491 (6)0.1706 (11)0.3578 (3)0.0436 (15)
H12A0.24080.28260.38970.052*
C130.3322 (6)0.2602 (11)0.3099 (3)0.0455 (16)
H13A0.35880.14080.28350.055*
C140.2546 (6)0.4380 (12)0.2704 (3)0.0523 (18)
H14A0.24000.57100.29440.063*
C150.3289 (7)0.6851 (15)0.1968 (3)0.058 (2)
C160.4170 (7)0.7047 (14)0.1476 (3)0.0594 (19)
H16A0.41470.83490.12480.071*
C170.4991 (7)0.5466 (15)0.1343 (3)0.062 (2)
H17A0.49990.41890.15820.074*
C180.5902 (6)0.5500 (11)0.0855 (3)0.0448 (15)
C190.6731 (7)0.3730 (13)0.0785 (3)0.0558 (18)
H19A0.67200.25240.10490.067*
C200.7586 (6)0.3706 (13)0.0325 (3)0.0527 (17)
H20A0.81180.24740.02750.063*
C210.7641 (6)0.5531 (13)0.0059 (3)0.0499 (17)
C220.6811 (6)0.7313 (13)0.0001 (3)0.0547 (18)
H22A0.68260.85200.02630.066*
C230.5952 (6)0.7300 (13)0.0457 (3)0.0534 (18)
H23A0.53990.85130.04980.064*
C240.8593 (8)0.7190 (19)0.0897 (4)0.088 (3)
H24A0.92510.68960.11740.132*
H24B0.88480.84950.06590.132*
H24C0.77230.74100.11340.132*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0890.0890.0890.0000.0110.000
C10.062 (5)0.131 (8)0.109 (7)0.030 (6)0.033 (5)0.042 (7)
O20.049 (3)0.071 (3)0.061 (3)0.011 (3)0.019 (2)0.012 (3)
C20.051 (4)0.126 (8)0.079 (5)0.008 (5)0.027 (4)0.054 (6)
O30.088 (4)0.104 (5)0.049 (3)0.037 (4)0.014 (3)0.006 (3)
C30.113 (7)0.090 (7)0.066 (5)0.025 (7)0.006 (5)0.001 (5)
O40.067 (3)0.060 (3)0.046 (3)0.009 (3)0.017 (2)0.005 (3)
C40.055 (4)0.060 (5)0.055 (4)0.001 (4)0.007 (3)0.009 (4)
O50.119 (5)0.050 (4)0.086 (4)0.014 (4)0.016 (3)0.008 (3)
C50.118 (8)0.143 (10)0.095 (7)0.048 (8)0.050 (6)0.023 (7)
O60.051 (3)0.052 (3)0.054 (3)0.008 (2)0.021 (2)0.010 (2)
C60.075 (5)0.052 (5)0.058 (4)0.030 (5)0.011 (4)0.001 (4)
O70.132 (5)0.074 (4)0.084 (4)0.025 (4)0.033 (4)0.005 (4)
C70.077 (5)0.069 (6)0.061 (4)0.003 (5)0.006 (4)0.010 (5)
O80.056 (3)0.046 (3)0.061 (3)0.005 (2)0.004 (2)0.000 (3)
C80.052 (4)0.059 (5)0.068 (5)0.002 (4)0.003 (4)0.005 (5)
O90.044 (2)0.049 (3)0.058 (3)0.005 (2)0.020 (2)0.009 (2)
C90.042 (4)0.051 (4)0.070 (5)0.000 (4)0.011 (3)0.000 (4)
O100.060 (3)0.042 (2)0.069 (3)0.009 (2)0.038 (2)0.006 (3)
C100.046 (4)0.058 (5)0.057 (4)0.002 (3)0.023 (3)0.001 (4)
C110.054 (4)0.042 (4)0.054 (4)0.001 (3)0.029 (3)0.000 (3)
O110.086 (4)0.044 (3)0.073 (3)0.012 (3)0.037 (3)0.003 (3)
O120.073 (3)0.074 (4)0.063 (3)0.023 (3)0.033 (3)0.015 (3)
C120.050 (4)0.033 (3)0.048 (3)0.002 (3)0.010 (3)0.005 (3)
C130.048 (4)0.043 (4)0.046 (3)0.006 (3)0.012 (3)0.011 (3)
C140.054 (4)0.047 (4)0.061 (4)0.011 (3)0.028 (3)0.021 (4)
C150.049 (4)0.073 (5)0.056 (4)0.018 (4)0.026 (3)0.010 (4)
C160.061 (4)0.063 (5)0.059 (4)0.016 (4)0.025 (3)0.002 (4)
C170.052 (4)0.089 (6)0.047 (4)0.001 (4)0.013 (3)0.005 (4)
C180.042 (3)0.049 (4)0.045 (3)0.006 (3)0.012 (3)0.002 (3)
C190.055 (4)0.060 (5)0.051 (4)0.006 (4)0.003 (3)0.003 (4)
C200.048 (4)0.058 (4)0.053 (4)0.004 (4)0.013 (3)0.004 (4)
C210.044 (3)0.062 (4)0.045 (4)0.002 (4)0.012 (3)0.005 (4)
C220.059 (4)0.053 (4)0.054 (4)0.002 (4)0.016 (3)0.010 (4)
C230.043 (4)0.066 (5)0.054 (4)0.001 (4)0.015 (3)0.001 (4)
C240.083 (5)0.127 (8)0.064 (5)0.001 (7)0.048 (4)0.002 (6)
Geometric parameters (Å, º) top
O1—C21.183 (9)O10—C151.366 (9)
C1—C21.475 (12)O10—C141.403 (7)
C1—H1A0.9600C10—C111.516 (9)
C1—H1B0.9600C10—H10A0.9800
C1—H1C0.9600C11—C121.518 (9)
O2—C21.358 (8)C11—H11A0.9800
O2—C131.456 (7)O11—C151.199 (8)
O3—C41.193 (8)O12—C211.372 (7)
C3—C41.450 (12)O12—C241.411 (11)
C3—H3A0.9600C12—C131.509 (8)
C3—H3B0.9600C12—H12A0.9800
C3—H3C0.9600C13—C141.525 (9)
O4—C41.367 (8)C13—H13A0.9800
O4—C121.448 (8)C14—H14A0.9800
O5—C61.182 (10)C15—C161.469 (8)
C5—C61.509 (10)C16—C171.315 (10)
C5—H5A0.9600C16—H16A0.9300
C5—H5B0.9600C17—C181.479 (8)
C5—H5C0.9600C17—H17A0.9300
O6—C61.365 (9)C18—C191.375 (9)
O6—C111.425 (7)C18—C231.396 (9)
O7—C81.253 (9)C19—C201.390 (8)
C7—C81.477 (10)C19—H19A0.9300
C7—H7A0.9600C20—C211.389 (10)
C7—H7B0.9600C20—H20A0.9300
C7—H7C0.9600C21—C221.376 (9)
O8—C81.305 (9)C22—C231.386 (8)
O8—C91.431 (8)C22—H22A0.9300
O9—C141.413 (7)C23—H23A0.9300
O9—C101.426 (7)C24—H24A0.9600
C9—C101.512 (9)C24—H24B0.9600
C9—H9A0.9700C24—H24C0.9600
C9—H9B0.9700
C2—C1—H1A109.5C10—C11—C12110.9 (5)
C2—C1—H1B109.5O6—C11—H11A110.5
H1A—C1—H1B109.5C10—C11—H11A110.5
C2—C1—H1C109.5C12—C11—H11A110.5
H1A—C1—H1C109.5C21—O12—C24117.3 (6)
H1B—C1—H1C109.5O4—C12—C13106.0 (5)
C2—O2—C13118.1 (5)O4—C12—C11110.3 (5)
O1—C2—O2121.4 (7)C13—C12—C11111.0 (5)
O1—C2—C1127.2 (7)O4—C12—H12A109.8
O2—C2—C1109.9 (7)C13—C12—H12A109.8
C4—C3—H3A109.5C11—C12—H12A109.8
C4—C3—H3B109.5O2—C13—C12108.3 (5)
H3A—C3—H3B109.5O2—C13—C14106.2 (5)
C4—C3—H3C109.5C12—C13—C14110.9 (5)
H3A—C3—H3C109.5O2—C13—H13A110.4
H3B—C3—H3C109.5C12—C13—H13A110.4
C4—O4—C12118.3 (5)C14—C13—H13A110.4
O3—C4—O4122.5 (7)O10—C14—O9106.4 (5)
O3—C4—C3126.3 (7)O10—C14—C13104.3 (5)
O4—C4—C3111.2 (7)O9—C14—C13108.4 (5)
C6—C5—H5A109.5O10—C14—H14A112.4
C6—C5—H5B109.5O9—C14—H14A112.4
H5A—C5—H5B109.5C13—C14—H14A112.4
C6—C5—H5C109.5O11—C15—O10123.4 (5)
H5A—C5—H5C109.5O11—C15—C16124.5 (7)
H5B—C5—H5C109.5O10—C15—C16112.1 (7)
C6—O6—C11118.1 (5)C17—C16—C15123.1 (7)
O5—C6—O6125.7 (6)C17—C16—H16A118.5
O5—C6—C5124.5 (9)C15—C16—H16A118.5
O6—C6—C5109.8 (8)C16—C17—C18127.0 (7)
C8—C7—H7A109.5C16—C17—H17A116.5
C8—C7—H7B109.5C18—C17—H17A116.5
H7A—C7—H7B109.5C19—C18—C23118.2 (6)
C8—C7—H7C109.5C19—C18—C17120.1 (7)
H7A—C7—H7C109.5C23—C18—C17121.8 (6)
H7B—C7—H7C109.5C18—C19—C20121.3 (7)
C8—O8—C9120.5 (6)C18—C19—H19A119.4
O7—C8—O8121.9 (7)C20—C19—H19A119.4
O7—C8—C7124.1 (8)C19—C20—C21119.6 (7)
O8—C8—C7113.9 (7)C19—C20—H20A120.2
C14—O9—C10112.6 (5)C21—C20—H20A120.2
O8—C9—C10112.0 (5)O12—C21—C22124.3 (6)
O8—C9—H9A109.2O12—C21—C20115.7 (6)
C10—C9—H9A109.2C22—C21—C20119.9 (6)
O8—C9—H9B109.2C21—C22—C23119.7 (7)
C10—C9—H9B109.2C21—C22—H22A120.2
H9A—C9—H9B107.9C23—C22—H22A120.2
C15—O10—C14117.9 (5)C22—C23—C18121.3 (7)
O9—C10—C9107.0 (5)C22—C23—H23A119.4
O9—C10—C11110.3 (5)C18—C23—H23A119.4
C9—C10—C11113.8 (6)O12—C24—H24A109.5
O9—C10—H10A108.5O12—C24—H24B109.5
C9—C10—H10A108.5H24A—C24—H24B109.5
C11—C10—H10A108.5O12—C24—H24C109.5
O6—C11—C10104.2 (5)H24A—C24—H24C109.5
O6—C11—C12110.1 (5)H24B—C24—H24C109.5
C13—O2—C2—O12.2 (13)O4—C12—C13—C14171.1 (5)
C13—O2—C2—C1169.5 (7)C11—C12—C13—C1451.3 (7)
C12—O4—C4—O32.7 (10)C15—O10—C14—O994.4 (7)
C12—O4—C4—C3176.6 (6)C15—O10—C14—C13151.1 (5)
C11—O6—C6—O55.5 (11)C10—O9—C14—O10176.0 (5)
C11—O6—C6—C5177.4 (6)C10—O9—C14—C1364.4 (6)
C9—O8—C8—O70.6 (11)O2—C13—C14—O1071.6 (5)
C9—O8—C8—C7179.3 (5)C12—C13—C14—O10170.9 (5)
C8—O8—C9—C10100.3 (8)O2—C13—C14—O9175.3 (4)
C14—O9—C10—C9172.6 (6)C12—C13—C14—O957.8 (6)
C14—O9—C10—C1163.1 (7)C14—O10—C15—O110.9 (10)
O8—C9—C10—O946.1 (8)C14—O10—C15—C16179.8 (6)
O8—C9—C10—C1176.0 (7)O11—C15—C16—C17175.3 (7)
C6—O6—C11—C10147.6 (6)O10—C15—C16—C175.5 (10)
C6—O6—C11—C1293.3 (7)C15—C16—C17—C18179.4 (7)
O9—C10—C11—O6172.1 (5)C16—C17—C18—C19178.2 (7)
C9—C10—C11—O667.7 (7)C16—C17—C18—C231.7 (11)
O9—C10—C11—C1253.6 (7)C23—C18—C19—C200.8 (10)
C9—C10—C11—C12173.9 (5)C17—C18—C19—C20179.2 (6)
C4—O4—C12—C13140.7 (6)C18—C19—C20—C212.1 (10)
C4—O4—C12—C1199.0 (6)C24—O12—C21—C220.3 (10)
O6—C11—C12—O478.9 (6)C24—O12—C21—C20178.8 (7)
C10—C11—C12—O4166.2 (5)C19—C20—C21—O12178.8 (6)
O6—C11—C12—C13163.9 (5)C19—C20—C21—C222.7 (10)
C10—C11—C12—C1349.0 (7)O12—C21—C22—C23179.7 (6)
C2—O2—C13—C12129.9 (7)C20—C21—C22—C231.9 (10)
C2—O2—C13—C14110.9 (7)C21—C22—C23—C180.6 (10)
O4—C12—C13—O272.7 (6)C19—C18—C23—C220.1 (10)
C11—C12—C13—O2167.5 (5)C17—C18—C23—C22180.0 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5A···O3i0.962.453.164 (12)131
C10—H10A···O5ii0.982.483.423 (9)160
C13—H13A···O11iii0.982.553.371 (8)142
C24—H24A···O8iv0.962.513.457 (10)171
Symmetry codes: (i) x, y1/2, z+1; (ii) x, y+1, z; (iii) x, y1, z; (iv) x+1, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC24H28O12
Mr508.46
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)9.972 (2), 6.0580 (12), 21.680 (4)
β (°) 97.19 (3)
V3)1299.4 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.40 × 0.10 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.959, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
2955, 2790, 1578
Rint0.062
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.070, 0.189, 1.02
No. of reflections2790
No. of parameters319
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.43, 0.40

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5A···O3i0.96002.45003.164 (12)131.00
C10—H10A···O5ii0.98002.48003.423 (9)160.00
C13—H13A···O11iii0.98002.55003.371 (8)142.00
C24—H24A···O8iv0.96002.51003.457 (10)171.00
Symmetry codes: (i) x, y1/2, z+1; (ii) x, y+1, z; (iii) x, y1, z; (iv) x+1, y+1/2, z.
 

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationEnraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
First citationLoganathan, D. & Trivedi, G. K. (1987). Carbohydr. Res. 162, 117–125.  CrossRef CAS Web of Science Google Scholar
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationYu, C. F., Liu, Z. F. & Cai, M. S. (1991). Chem. Res. Chin. Univ. 12, 349–350.  CAS Google Scholar

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